Date Start?
by Crilbyte
Summary: Papyrus has invited you to date! Only problem is... he doesn't know what all that entails. But that's okay, you'll help him out with that, right? Oh, and be careful, you never know when Sans might be getting home.
**Title:** Date

 **Rating:** M

 **Words:** 4244

 **Tags:** Undertale, Papyrus, first time, Female Main

(If you need anything else tagged, please tell me!)

 **Summary:** Papyrus learns "Whatever it is that people do when they date."

 **Notes:** This is the first part of a two part lemon-oneshot (I know, old terms, I've been at this a while. Veteran sex story fanfiction writer here, showing off her age) first part being about Papyrus, second part including something different, you'll know by the end what…

No Spoilers…

Keep Reading

 **Date** **(part 1)**

 **Reader/Papyrus**

Undertale

You take a few steps backwards, getting one last look at Snowdin before continuing on your journey home. You can feel the cold wind whip your hair into a frenzy and turn around, facing the forest ahead of you. With a determined look, you put a foot forward, but the further you go the thicker the air becomes. It goes from a winter wonderland to a blizzard in moments, you put your hand in front of your face to try and keep your eyes clear, but you can't even see a foot in front of you anymore. The cold sinks under your skin, making you almost numb; the sound of the snow crunching beneath your feet is the only sense still seeming to work. Then you see a shadow a little ways in front of you. Stopping and squinting, you try to make out what it is, fear tickling in the back of your throat, before a booming, familiar voice breaks the screams over the storm.

"HUMAN!" you hear Papyrus yell out, dropping your hand as you raise an eyebrow. What is this silly skeleton up to now? "Allow me to tell you some complex feelings. Feelings like… the joy of finding another pasta lover. The admiration for another's puzzle solving skills. The desire to have a cool, smart person think you are cool. These feelings…" He takes a meaningful pause before continuing, "These must be what you are feeling right now! I can hardly imagine what it must be like to feel that way. After all, I am very great! I don't ever wonder what having lots of friends is like. I pity you… Lonely human… Worry not! You shall be lonely no longer! I, the GREAT Papyrus, will be your…

"No… No! This is all wrong! I can't be your friend! You are a human! I must capture you! Then, I can fulfil my lifelong dream! Powerful! Popular! Prestigious! That's Papyrus! The newest member… of the royal guard!"

The snowstorm seems to clear once he finishes his speech and you take a few steps closer to him, but he doesn't move. Papyrus blocks your way!

"Nyeh heh heh!" He laughs. "I can't let you pass! I will capture you!"

"Why?" you ask.

"Because if I capture a human I can become one of the Royal guard!"

"You aren't one now?"

"No, not yet, but I will be!"

"Why do you want to be one so badly?"

"Because they're strong and popular and have a million friends!"

"You look plenty strong now, why do you need them? Besides, I've seen the royal guard, your outfit is way cooler than theirs."

"No way! Theirs is way cooler, and once I have you, after I capture you, I'm sure that Undyne will be so happy, they'll definitely give me a place in the guard!" Papyrus strikes a heroic pose and grins. The sight of it makes you giggle.

"Have me? Capture me? That sounds like fun," you say with a wry smile.

This gave Papyrus pause. "What!? Are you fl-flirting!? So you finally reveal your ultimate feelings! W-well! I'm a skeleton with very high standards!"

You cross your arms and think a moment before getting an idea. "I can make spaghetti?"

Papyrus's jaw drops and he throws his hands to the sides of his face, eyes bulging. "OH NO! YOU'RE MEETING ALL OF MY STANDARDS! I guess this means I have to go on a date with you?"

You blink and widen your eyes, "Oh, a date huh?" you let a smile cross your face, "That sounds kinda nice actually."

A blush forms over his boney face. "Let's date l-later! After I capture you!"

"You still want to capture me?" you ask, but he doesn't seem to hear you. He's too busy thinking about what to wear for his date.

"Papyrus?" you call a little louder.

"Oh, yes!" he shakes his head and gives you a determined look. "Right! See if you can dodge this attack!"

Suddenly there are bones flying at you. You manage to dodge them relatively easily, but it's still a shock. When he stops he waits as if expecting something. After a long awkward silence he asks, "Um, aren't you going to retaliate?"

You raise an eyebrow, "What? No?"

"So you won't fight? Then let's see if you can handle my fabled BLUE ATTACK!"

Then, once again, there are more bones flying at you, only this time they seem to be all painted blue. You cringe, raising your hands in defense and stand perfectly still. When you open your eyes you realize not one hit you, but when you look down at your hands you see that they are now covered in a spotty layer of blue paint.

You look up to see Papyrus standing triumphantly with his hands on his hips. "You're blue now. That's my attack. Nyeh heh heh heh heh heh!" he throws his head back in a roar of laughter.

Your eyebrows fall into a frustrated look as you try to rub some of the paint off on your skirt. "Jeeze Papyrus, really?" you scoff.

Meanwhile, Papyrus is whispering to himself, "Will anyone like me as sincerely as you? Someone like you is really rare… And dating might be kinda hard…" he mumbles, wringing his hands at this new realization, "After you're captured and sent away."

His thoughtful face makes you worry, "Papyrus are-"

He cuts you off, "UGH! Who cares!?" he says, shaking his head back and forth, "Give up!" he yells with new fervor, "Give up or face my special attack!"

You plant your feet and give back a determined look. "No."

"I'm not joking around!" Papyrus warns, holding a very large bone in a throwing position, "Not long till I use my special attack!"

You keep your stance, not moving an inch.

"Last chance!"

You stare him down.

"I'm gonna do it!"

You refuse to relent.

His expression falters a moment before dropping the bone to the ground next to him. A dog seemingly comes out of nowhere to snatch the bone and run off. Papyrus watches, stunned for a moment before regaining himself. "That's fine, probably better this way! It's clear you can't defeat me!" he says, resting his hands on his hips once again. "Yeah! I can see you shaking in your boots! Therefore I, the GREAT Papyrus, have elected to grant you pity! I will spare you, human! Now's your chance to accept my mercy!"

Your face slights up just the slightest bit. "Really? Okay." You smile and settle into a more relaxed position.

Papyrus's shoulders sink and in a regretful voice he lets out a few sullen words, "I'll never make friends…"

"Papyrus…" You take a few steps forward, reaching out towards him, "I'll be your friend?"

"Really!?" he yells, immediately cheering up. "We haven't even had our first date yet, and I've already hit the friendzone! Who knew that all I needed to make friends was to people awful puzzles and then fight them!? You've really taught me a lot. I hereby give you permission to pass!" he says with a grin. He closes the distance

"Thank you very much!" you say, excitedly.

"Well, I guess I'll see you around then." Papyrus waves and only manages to take a few steps to get around you before you grab his arm.

"Wait," your voice a little louder than you'd intended. Papyrus raises an impossible eyebrow at your outburst. "I thought we had a date?" you ask.

His eyes light up, "You mean it? You're still up for that?"

You nod quickly.

"Oh, well then! Onward! I, the GREAT Papyrus, will take you to one of my FAVORITE places, I'm there ALL THE TIME!"

He grabs your hand in his and guides you back to Snowdin. You look down at your grasped hands and smile a shy smile. It's hard to imagine. You had been sad, hopeless, so many times. It was only a few hours ago that you had left Toriel and felt scared of the coming unknown.

Only a few days before that did you fall down the hole that brought you here, having lost your whole world, everything you knew. Only a time ago, you were alone and scared. But now you have friends. Two silly skeleton friends, but friends nonetheless. You feel happy, and at home with them. Papyrus looks back and smiles at you, making you blush a little.

"Here it is!" he lets go of your hand and throws them in the air in a 'ta-da' like fashion. "This is my house!"

You walk closer, excited, but also nervous. Papyrus opens the door and motions for you to enter, so you do, looking around at the cozy house as he shuts the door behind you.

"This is where I live, with Sans of course! Over there is the kitchen, and this is the living room." Papyrus starts rambling, giving you a very rushed tour of the house. "That over there is Sans's pet rock, he never remembers to feed it… And up there on the right is Sans's room! I don't think he's ever heard of a vacuum before, because it is gross in there!

"And that door at the top of the stairs, that's my room! If you're done looking around, we can go in and do…" he paused, squinting his eyes and looking to the ground, "Whatever it is that people do when they date." You giggle at him and he starts of the stairs.

You follow him, still letting your eyes roam. It was a nice house for two skeletons. Not that they couldn't have a nice home, you'd just never considered skeletons living anywhere, you guess. It's an odd concept. You walk into Papyrus's room and the first thing to catch your eye is his bed. Sitting in the corner of the room was a red racecar bed, a fire emblem on the side, and orange and yellow sheets to match.

"Woah," you let out, walking slowly towards it and touching the sheets. They're very soft.

"That's my bed!" Papyrus comments, walking over and sitting on it. "If I ever get to the surface I'd like to drive it down a long hallway. Of course, that's just a dream, so instead I just cruise while I snooze."

You laugh at his words. "You mind if I sit with you?" you ask.

"Not at all!" he comments, patting next to him.

You crawl up and sit next to him with your knees crossed.

"Well, here we are! On our date! I've actually never done this before… but that's okay! You can't spell 'prepared' without several letters of my name!" Papyrus opened a drawer on his bedside table and began to rummage around before shouting "Ah-Ha!" and pulling out a book. "I snagged an official dating rulebook from the library! We're ready to have a great time! Let's see, step one…"

"Hey," you try to grab his attention.

His nose is deep in the book and he doesn't hear you, he just continues mumbling to himself.

"Papyrus," you say with a laugh. When he still doesn't answer you reach forward and grab the book, setting it on the bed next to you.

"Hey," he raises a brow at you.

"You don't need a book to have a good date." You give him a reassuring smile.

"I don't know, I've never done this before so I don't really know what to do…"

"Here, I'll start. How about I tell you a bit about myself?"

"That sounds like a good start!" He agrees.

You give him a little brief description of yourself; your name, interests, hobbies and such. He listens, hanging on your every word seemingly enthralled.

"So what about you? You have anything you like to do? Anything you're good at?" you ask, giving him somewhere to start.

"I'm good at cooking, but you knew that…" the rubs a bony finger on his chin, deep in thought for a moment before becoming excited and throwing his hand in the air. "I know! This is something good!" he turns to face you and grins. "I can do magic!"

You're slightly confused. You let your head fall to one side and say, "Magic? Like, card tricks?"

Papyrus's hands are suddenly shaming violently in-between the two. "Nononononono! MAGIC! REAL magic!" he looks away and raises his hands, concentrating.

You watch in anticipation, not sure what's going to happen, if anything. At first nothing _does_ happen. But that changes quickly. Papyrus's right eye begins to glow orange and across the room two robotic figurines begin to float into the air.

"Woah!" you shout out, crawling top the edge of the bed and watching as they begin to dance around in the air. "How do you do that!?"

"Sans taught me!" he says proudly, "I can do more tricks! Sans taught me how to create things, watch!" he places the figures softly back on the table and then in the center of the room, a strange orange glow begins to swirl, filling up more and more space until there it takes the shape of a little lion.

You watch with wide eyes as it prances about the room. Out of the corner of his eye Papyrus sneaks a glance at you, grinning widely at your happy face. He wiggles his fingers and the lion runs up the wall and onto the ceiling before doing a little flip and dissipating.

You erupt into an applause, laughing and smiling at him. "Papyrus! That was so cool! What else can you do?" you ask.

"Well, I can make a fake body?" he suggests, giving you an inquisitive look, wondering if you're still interested.

"Show me!?" you yell.

"Okay!" Papyrus stands and holds his arms out, the orange glowing substance filling his body slowly, until he was completely engulfed. You watch with wide eyes as it shapes itself around his bones and formed a chest, hands, legs, even a face around his skull.

You sit there, doe eyed, as Papyrus does a little spin. "Ta-da! What do you think? I can even use it for armour if I really need it!" he does one last pose before letting the glow recede until there's none left. He then takes a seat next to you once again.

"Papyrus! Seriously, that is so cool! How do you have magic!? I wish I could do all that!" you yell, waving your hands wildly as you speak.

"What?" he asks, "What do you mean WISH? You don't have magic? EVERYONE has magic!" he scoffs.

"No, humans don't have magic. We're pretty boring."

"That's weird? I don't think I've ever met someone who couldn't do magic. Maybe you just need to learn?" he crosses his arms contemplatively.

"Learn it? Does it not come naturally to you?" you ask, fully engulfed in this new conversation.

"Oh! Yes of course! Sans has been teaching me since we were little! He's got MUCH more of an aptitude for it than I," he pauses, stumbling over his own words a moment, "though I am better at a great many things!"

You laugh at his self-conscious exclamation. "I would love to learn. Did Sans teach you all those tricks?"

"All but the lion one! I made that up on my own." Papyrus raises his chin, obviously proud of himself.

You didn't want the fun to end so you attempt to egg him on a little longer. "Well, what else has Sans taught you?"

He rubs his chin a moment before throwing his hand up once again, "Oh, okay, I think I have one. But…" he pauses giving you an embarrassed look, "he's told me not to use it."

"Not to use it? Why? Is it dangerous?"

"I don't believe so. Actually, I'm not sure what the purpose of it even is. Just that Sans told me that he'd teach me at a later date. One that has not come yet."

"Well, if it's not dangerous, show me. I might be able to help!" you suggest, though you're pretty sure you'll be of no help at all. Honestly you just want to abate your curiosity.

"Oh! GOOD IDEA!" Papyrus yells happily. "Yes! Then I can show Sans and he'll be proud!" Papyrus looked very excited now.

"Yea, I bet he would. He's a good brother!"

Papyrus began to wring his hands nervously, "So, if you think you understand it…you promise to help me learn?" he asked.

"Definitely," You say with a big smile.

"Okay, here it goes."

You stare intently as Papyrus closes his eyes for a moment, when they open back up his right eye is once again glowing orange. He raises his hand and does a small motion with it and then nothing else. You sit patiently, waiting, but nothing happens.

You raise an eyebrow and question him, "You gonna do it?"

"It's done."

"It's…" you pause, looking around the room. Your eyes scan around you before coming to a halt on Papyrus's clothing. Your eyes grow as the realization sets in. "Oh," you say.

"What?" he asks, sweat beading on his brow, "Do you know what it's for?"

You slowly nod. "Yes. I'm pretty sure I know what it's for," you say, your voice flat.

"Well?" he asked, motioning with his hands, "You said you'd help me, right? You promised?"

Without making eye contact, without looking away at all, you say, "So, you know how you said you didn't know what people do on dates, so you had to get that book?"

"Yes?"

"Well…" you lean forward, placing a hand on the sheets to hold yourself up, "This spell, um, is probably to help assist someone of your…body type…with that process."

"Oh, goodie!" Papyrus clapped, "Then this is perfect! Show me how it helps?"

You finally broke your stare and looked up at him, "You're sure?"

"Yes, please!" he insists.

"Okay, here we go." You lean a little closer to him, the hand not holding you in place reaching out towards him. You gingerly grab at his waistline, gripping the costume bottoms and pulling them down slowly to reveal a very erect glowing orange penis.

The moment your eyes lock onto it a blush forms on your face.

"Are you okay?" Papyrus asks, completely unfazed by the situation.

"Yes, just a little flustered," you pause and look up to meet his gaze, "So you really don't have any idea what this is?"

"NOPE!" he exclaims, almost proudly, "NONE AT ALL!"

You raise a curious eyebrow at him as he laughs out loud a moment. He's always been a very outspoken and loud individual, but that's one of the reasons you came to really like him in the first place. Although you never seemed to be able to hit back enough to give him pause; and then today happened. There you sit, the universe holding out a silver platter in front of you, with the trump card of all trump cards. You have the guide in your hands, and all you have to do now was hit his weak points.

This is gonna be fun.

"You ready?"

"Indeed human!"

"Alright," you exclaim, "Here we go then!" you lean forward, taking hold of this new addition to the already large pile of bones, and – without giving him a moment to understand – lean down, letting the full length of your tongue press against him, dragging it all the way from the base to the tip.

The subsequent reaction was much better than anything you could have hoped for.

Papyrus lets out a surprised shuddering yelp, his hands flying up into the air before quickly grasping the shoulders of your shirt tightly in his fists. His eyes grow wide before snapping shut as he lets out another groan, his breath now heavy. This very honest reaction makes you warm deep down and you gladly continue, pursing your lips tightly and taking him into your mouth slowly.

"WAITWAITWAITWAITWAIT!" Papyrus yells out, his grip tightening on you, but you don't stop. You move slowly, up and down on him, having fun with it - playing around inside your mouth with your tongue, seeing just how deep you can take him. His breathing is erratic, switching from short gasps to strange moans, and sometimes you hear him stop entirely, holding his breath. In his confusion he pushes himself back until his shoulders hit the wall behind him, but you don't let him escape. After one last long stroke you pick yourself up, giving it just a few more short licks – causing Papyrus to twitch at each one – before looking up at him.

Between breaths he manages to push out, "What are you doing? What…what was that?"

You grin, pulling yourself closer to him, so you're almost in his lap. "Was it bad?" you ask.

"I, Y-, N-NO," he stops, closing his eyes in thought, "I don't know!"

"Did you dislike it?" you ask sincerely.

"No, it was…overwhelming, but not…bad," he admits.

"I can show you other things?" you trail your finger up from his femur to his pelvis, then moving up to his ribs, sliding it up until you reached his chin and pulled your finger across it, flicking it up a bit.

You're confidence level was skyrocketing, which made absolutely no sense since you usually were just a big ball of nerves; but here, with him, it felt different. It's a strange sensation; a kind of inverse correlation. The redder he gets, the more confident you feel. You could feel the smirk on your lips, the way you were holding yourself, the half opened sensual eyes, it all flowed through you as it if came naturally. You ponder it for only a moment to find… you love it.

Your smile grows slightly, showing more teeth as Papyrus struggles to maintain his composure. "If you want…I can show you something even better…Would you like that?"

At first he doesn't look like he's going to answer, but then he gives a small nod and you comply. Papyrus stares at you as you lean closer and closer, your hands softly touching his shoulders and humerus. You kiss at his neck and clavicle, sneaking your tongue out and trailing it across causing him to shiver and let out a quick and quiet yip. Hands roaming, grazing different parts of him, his rips, sternum, the sides of his face; you share this passionate moment and then look back up at his face. His eyes – though just empty sockets – seem glazed over, he's enjoying himself.

You scoot yourself forward so you're sitting on his lap, your ankles hooked on his femurs and his warmth resting on your stomach. His hands find their way to your waist as yours wrap around his neck, "You ready?" you ask, "I'm gonna do something, and it's gonna feel really good, alright?"

Papyrus nods once again, though a little harder this time.

"Okay, here we go." You reach down with your left hand, leaving the other cradled on the back of his neck, and lift yourself up, pulling your underwear to the side and positioning him at your opening. Once the tip is in place you return your hand to its double and smile before slowly lowering yourself onto him.

His reaction is instantaneous. A loud and surprised moan escapes his teeth as his grip on your waist tightens and his head falls back. The honesty in his response sends a pleasurable shiver down your spine and you pull yourself back up, ready to see it again. When you lower yourself this time you do it a little quicker, pulling yet another juicy reaction from him.

"Was I right," you ask, slowly picking yourself up and down, "You feel good?"

Papyrus opens his mouth to answer but only chokes out a, "Yes! It feels-!" before you pick up the pace and cut off his words with a new flood of moans. His hands relax each time you raise and tighten with each drop. While his eyes are closed you take the opportunity to pull yourself up to his face and leave a little kiss on his teeth.

He opens his eyes and stares at you, causing you to blush and slow down a bit. When he doesn't look away you drop your gaze and stop completely, sitting there on his lap.

"Was that-?" he begins to ask, raising a hand to his mouth.

You don't answer, but instead shrug.

You feel his finger on your chin as he pulls your face up to meet his. With one hand still firmly on your hip, he pulls you close and presses his skeleton mouth onto yours. Your eyes shoot open and you can feel the heat as all the blood rushes to your face. When he pulls back he smiles at you, "You really do care about me, don't you?" he asks, quieter than you ever thought he could be.

You nod, "Of course. I wouldn't lie. I care about both of you."

Papyrus touches his forehead to yours and says, "I'm glad," before pressing against your lips once more.

Abruptly, the sweet moment is ruined as you hear a new voice in the room.

"Well, well, well! This was the last thing I expected to see when I came home."

Both yours and Papyrus's eyes grow wide as you turn to see Sans standing in the doorway, leaned against the frame, with his arms crossed and a large smirk on his face.


End file.
